Courtney played Eric, one of the leaders of the factionDauntless, in the film Divergent (2014). In February 2014, it was announced he would play Kyle Reese in Terminator Genisys.[8] While filming for Terminator Genisys, Courtney will also be shooting for The Divergent Series: Insurgent, the sequel to Divergent, in which he will reprise his role. Filming on Terminator Genisys began in April/May 2014,[9] and be released on 1 July 2015[10] while filming on Insurgent began on May 2014 with a release date of 20 March 2015.[11]

Courtney's films in 2014 included Unbroken, where he played Hugh "Cup" Cuppernell, and The Water Diviner, in which he starred as Lt. Col. Cecil Hilton.[12]

Courtney provided backing vocals on the Pinch Hitter song "All of a Sudden" from their debut album, When Friends Die in Accidents.[13][14]